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Stigmasterol

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-S3027

  • Specification : 98%

  • CAS number : 83-48-7

  • Formula : C29H48O

  • Molecular Weight : 412.7

  • PUBCHEM ID : 5280794

  • Volume : 25mg

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Catalogue Number

BF-S3027

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

412.7

Appearance

White crystalline powder

Botanical Source

Heracleum hemsleyanum

Structure Type

Others

Category

Standards;Natural Pytochemical;API

SMILES

CCC(C=CC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(C)C

Synonyms

(24S)-5,22-Stigmastadien-3b-ol/Stigmasta-5,22-dien-3-ol, (3β,22E)-/STIGMASTEROL (STIGMASTERIN)/(24S)-Stigmast-5,22-dien-3β-ol/STIGMASTEROL(P)/Wulzen anti-stiffness factor/Guinea-pig-anti-stiffness factor/SULFISOXAZOLE/Stigmasta-5,22-dien-3-ol, (3β,22E)- (9CI)/Stigmasta-5,22-dien-3β-ol/Stigmasterol/δ5,22-Stigmastadien-3β-ol/Anti-stiffness factor/(3β,22E)-Stigmasta-5,22-dien-3-ol/Stigmasta-5,22-dien-3-ol, (3β)-/Stigmasta-5,22-dien-3-ol, (3β,20R,22E,24S)-/Stigmasta-5,22-dien-3β-ol (8CI)/Stigmasta-5,22E-dien-3β-ol/isofucosterol/stigmasta-5,22-dien-3-b-ol/Stigmastero/STIGMASTA-5,22-DIEN-3-OL,(3B,22E)-/Stigmasterin/(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,3E,5S)-5-Ethyl-6-methyl-3-hepten-2-yl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol/(3β,20R,22E,24S)-Stigmasta-5,22-dien-3-ol/3b-Hydroxy-24-ethyl-D5,22-cholestadiene/δ5-Stigmasterol/24S-ethylcholest-5,22-dien-3β-ol/stigmasta-5,22-dien-3-β-ol/β-Stigmasterol/(24S)-5,22-Stigmastadien-3β-ol/(3b,22E)-Stigmasta-5,22-dien-3-ol/5,22-stigmastadien-3β-ol/(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,3E,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol/PHYTOSTEROL/(24S)-24-Ethylcholesta-5,22-dien-3β-ol

IUPAC Name

(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

Applications

Stigmasterol is a plant sterol which has been focused on the cholesterol-lowering activity and is valued as an anti-stiffness factor in the therapy of rheumatic diseases.

Density

1.0±0.1 g/cm3

Solubility

Methanol; DMSO

Flash Point

219.4±13.7 °C

Boiling Point

501.1±19.0 °C at 760 mmHg

Melting Point

165-167 °C(lit.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2906190000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:83-48-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30140696

Abstract

The therapeutic potential of stigmasterol, a natural steroid alcohol with established immune-modulatory properties, was assessed on allergic cutaneous responses. We examined its suppressive effect on immunoglobulin E (IgE)-mediated active cutaneous anaphylaxis (ACA), compound 48/80 (C48/80)-induced pruritus, and irritant dermatitis induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). Stigmasterol at 10-100 mg/kg significantly inhibited ACA with reduction in reaction area and concentration of the extravasated Evans blue dye. Given at 50 and 100 mg/kg, stigmasterol significantly inhibited C48/80-induced scratching behaviour when compared to saline-treated C48/80-injected control. Skin histopathology of injected sites confirmed that stigmasterol reduced mast cell trafficking and degranulation associated with C48/80-induced pruritus. Stigmasterol controlled inflammatory features such as ear skin oedema and neutrophilia and also reduced serum levels of TNFα induced by topical application of TPA. Epidermal layer thickening and inflammatory cell infiltration of ear skin tissue were significantly reduced by stigmasterol. Taken together, stigmasterol demonstrates significant potential as a molecule of interest in allergic skin disease therapy.

Title

Stigmasterol Alleviates Cutaneous Allergic Responses in Rodents.

Author

Antwi AO1, Obiri DD1, Osafo N1, Essel LB1, Forkuo AD1, Atobiga C2.

Publish date

2018 Jul 24

PMID

28710626

Abstract

Stigmasterol is a phytosterol contained in Kraft mill effluent that is able to increase over 100% after aerobic biological treatment. This compound can act as an endocrine disrupter as its structure is similar to that of cholesterol. Furthermore, stigmasterol contained in Kraft mill effluent shows high toxicity (25-fold that of β-sitosterol) to aquatic organisms such as Daphnia magna (24-48 h). However, the operation of the aerobic treatment and biomass adaptation could be affecting their removal. The performances of activated sludge (AS), aerated lagoon (AL), and moving bed biofilm reactors (MBBR) are compared for removing stigmasterol contained in Kraft mill effluent. The AL operates at a hydraulic retention time of 6 h and removes up to 90% of phytosterols. So, a 96% of stigmasterol is removed by AL when the sterol retention load is 0.6 mg/L/day. However, stigmasterol concentrations increase from 29% to 37% at a low stigmasterol load rate (0.2 mg/L/day). On the other hand, the stigmasterol is removed between 65% and 87% by an AS under a hydraulic retention time of 3 h. Moreover, a 100% of stigmasterol can be removed by the MBBR when the hydraulic retention time is 2 days.

KEYWORDS

Activated sludge; Aerated lagoon; Kraft mill effluent; Moving bed biofilm reactors; Stigmasterol removal

Title

Stigmasterol Removal by an Aerobic Treatment System.

Author

Chamorro S1, Xavier C1,2, Hernandez V3, Becerra J3, Vidal G4.

Publish date

2017

PMID

30305244

Abstract

OBJECTIVE:
To investigate and compare the effects of two common dietary phytosterols, stigmasterol and β-sitosterol, in altering lipid metabolism and attenuating nonalcoholic fatty liver disease (NAFLD).

METHODS:
Stigmasterol and β-sitosterol were administered to mice at 0.4% in a high-fat western-style diet (HFWD) for 17 weeks.

RESULTS:
Stigmasterol and β-sitosterol significantly ameliorated HFWD-induced fatty liver and metabolic abnormalities, including elevated levels of hepatic total lipids, triacylglycerols, cholesterol and liver histopathology. Both phytosterols decreased the levels of intestinal bile acids, accompanied by markedly increased fecal lipid levels. In addition, they altered the expression of genes involved in lipid metabolism. β-Sitosterol was less effective in affecting most of these parameters. Lipidomic analysis of liver and serum samples showed that stigmasterol prevented the HFWD-induced elevation of some di- and triacylglycerol species and lowering of some phospholipid species. Stigmasterol also decreased serum levels of ceramides.

CONCLUSION:
Stigmasterol and β-sitosterol, at a dose corresponding to that suggested for humans by the FDA for lowering cholesterol levels, are shown to alleviate HFWD-induced NAFLD. Stigmasterol was more effective than β-sitosterol, possibly because of its suppression of hepatic lipogenic gene expression and modulation of circulating ceramide levels.

Copyright © 2018 Elsevier B.V. All rights reserved.

KEYWORDS

Cholesterol; Fatty liver; Lipidomics; Mice; Stigmasterol; β-Sitosterol

Title

Intake of stigmasterol and β-sitosterol alters lipid metabolism and alleviates NAFLD in mice fed a high-fat western-style diet.

Author

Feng S1, Dai Z2, Liu AB3, Huang J4, Narsipur N3, Guo G5, Kong B5, Reuhl K5, Lu W6, Luo Z7, Yang CS8.

Publish date

2018 Oct